The internet is currently the most versatile medium of communication. It remains true to its heritage having been designed by the US military to withstand a nuclear attack. At conception it was designed to route around censorship and controls. It however, now functions in the civilian world in which laws and regulation are the norm. The Australian High Court attempted to put in place regulations and principles on on-line Defamation in Dow Jones v Gutnick (Gutnick). However the borderless nature of the internet has brought to the fore, the complexities involved in developing internet legal principles. This is in a world still fraught with inherently different legal systems, with one foot placed on globalisation and the other clinging on to sovereignty. A clash between free speech and reputation was the result of Gutnick and a renewed offensive is in the offing. The pertinent question explored in this discourse is whether the defamation principles reiterated and established by the High Court of Australia in Gutnick will survive.